Bryan, there are many people out there who don't judge by what you have.....many.......personally, i'd rather meet a hard worker and someone who can think for themselves than someone who sits around while the interest piles up.........
painting is very, very hard. it isn't easy. i have a friend who won't let me do anything but prime and very little of that. and i can make teensy tiny jewelry....but put a brush in my hand and "bar the door".......property management is an excellent field to be in these days. there are always going to be more and more renters and having the ability to manage property, know the values, etc. will do you very well.........
don't be so hard upon yourself.....we all do it. i do.....and we need one another to jab us

at times and tell us to "get over it".....
and it also sounds to me as if your boss is being kind....not overly bossy. i'd love for someone to have my back......xoxoxo pat